1. Field of the Disclosure
This disclosure relates to isomeric alkadienals and their use in perfume compositions. In particular, this disclosure relates to isomeric undecadienals, dodecadienals and tridecadienals and their use in perfume compositions. More, in particular, this disclosure provides cis- and trans-isomers of 4,8-undecadienal, 4,9-dodecadienal and 4,10-tridecadienal for use in perfumery applications.
2. Description of the Related Art
Various alkenals and alkadienals having 10 or more carbon atoms are known as fragrance materials or flavorings. For example, S. Arctander in “Perfume and Flavor Chemicals”, names 2,4-decadienal and 2-decenal as fragrance materials but without any reference to cis or trans configuration, and 8-, 9- and 10-undecenal, of which 8- and 9-undecenal have the cis configuration. In U.S. Pat. Nos. 3,821,421 and 3,686,003, it is reported that both cis-4-decenal and cis, cis-4,7-tridecadienal and other polyunsaturated aldehydes containing 11-17 carbon atoms are suitable for imparting an aroma of chicken meat to foodstuffs.
Other dienals such as 2E,4E-decadienal, 2E,4E-undecadienal and 2E,6Z-dodecadienal have been reported and used in chicken meat flavor preparations. Further to this, Gerard Moschiano (Perfumer & Flavorist 23, No. 3, 55, 1998) describes the alkyl dienal, 2,4-decadienal as having fatty, chicken, fried, citrus, coriander and brothy odor. More recently, Delort et al reported the identification and synthesis of several alkadienals found in extracts obtained from distinct parts of chicken (J. Agric. Food Chem. 2011, 59, 11752-11763). For this reason, it was not to be expected that this class of compounds would be suitable as raw materials for perfume compositions.
In U.S. Pat. No. 3,928,402, a method of synthesis is described for γ-δ-unsaturated carbonyl compounds including aldehydes. However, only compounds with a 2,4-diene system and/or an ester or keto group are disclosed.
In U.S. Pat. No. 3,920,752, it is reported that certain γ-δ-unsaturated aldehydes are valuable fragrance materials. From the structural formulae, however, only branched C-11 dienals with a trans-double bond at carbon 4 are disclosed. In U.S. Pat. No. 4,687,599, it is reported that cis,cis-4,7-decadienal, cis,cis-4,7,9-decatrienal and 4,7,12-tridecatrienal are useful fragrance materials but the trans-isomers are excluded.
None of these publications give any indication that in particular the geometric isomers of 4,8-undecadienal, 4,9-dodecadienal and 4,10-tridecadienal would be suitable ingredients for perfume formulations.
There is an ongoing interest in the fragrance industry to use new compounds that enhance or improve odor character and impart new notes to help perfumers create exciting new fragrance experience desired by consumers.
The present disclosure provides many advantages, which shall become apparent as described below.